Vacation Contests
This list contains many contests for Trip that are open world wide. If you are looking for local contests checkout the contest locale archive.
Win a five-night stay at an Embassy Suites hotel and a $500 gift card in the 40th Anniversary Milestone Sweepstakes! Share your recent or upcoming milestone for a chance to win.
Contest ends: May 31, 2024
Entry limit: Daily Entry
Eligible for USA ResidentsWin a 2-night stay for a family of four at a Discovery Cove partner hotel property. It's worth $4,600 and could be yours with the Guy Harvey Discovery Cove Summer Giveaway. Enter now!
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for USA ResidentsWin an unforgettable My Jolly Summer Giveaway Prize, including a two-night stay in Ocean City, MD, and four passes to Jolly Roger Amusement Park. Valued at $1,000, this prize is your ticket to creating cherished summer memories! Transportation not included.
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for USA ResidentsWin one of ten prizes: a five-night stay at an Embassy Suite hotel and a $500 gift card. Share your recent or upcoming milestone to enter. Winners will be selected through random draw.
Contest ends: May 31, 2024
Entry limit: Daily Entry
Eligible for USA ResidentsEnter now for an opportunity to win one of four prizes of 200,000 HawaiianMiles reward miles, worth $6,000, in the 31 Days Of Lei Sweepstakes by Hawaiian Airlines. Let your dream vacation begin!
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for USA ResidentsWin a free ferry trip on the Coho Ferry in the Black Ball Ferry Line Calendar Contest! Submit your best photo of the iconic ferry for a chance to win one of 17 prizes.
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for Canadian Residents(Except: QC)Enter the Sandals - Jamaica Is Calling Sweepstakes and secure a four-night all-inclusive stay at an exquisite Sandals resort in Jamaica, worth $6,835. Airfare not included, but agree to receive emails from eight companies for your chance to win! 🌴🏝️
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for USA Residents(Except: RI)Enter the Embassy Suites by Hilton 40th Anniversary Milestone Sweepstakes for your chance to win a 5-night stay at any Embassy Suites location worldwide and a $500 travel stipend. Five additional winners will receive a 2-night stay, and two winners will receive a carry-on suitcase and 1-night stay.
Contest ends: May 31, 2024
Entry limit: Daily Entry
Eligible for USA ResidentsWin a dream vacation to the Virgin Islands with a 4-night stay for two at The Buccaneer Beach & Golf Resort in St Croix, daily breakfast and a beach dinner worth $6,700. Airfare not included, sign up for newsletters to enter.
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for USA Residents(Except: RI)Win a 4-week dream vacation worth $18,242 with Wyndham Rewards points and bonus cash in the TMZ/TMZ Live - Pick Your Destination Sweepstakes. Watch TMZ on TV or TMZ Live weekdays for the secret word to enter!
Contest ends: May 31, 2024
Entry limit: Daily Entry
Eligible for USA ResidentsEnter now for a chance to win one of two prizes - a 3-night trip for two to the Essence Festival of Culture in New Orleans from July 5-7, 2023, valued at $4,745. Don't miss out on this opportunity to immerse yourself in the rich culture and music of the city!
Contest ends: May 31, 2024
Entry limit: Daily Entry
Eligible for USA Residents(Except: RI)Win an unforgettable experience! Enter now for a chance to win a trip for two to Minneapolis with VIP tickets to attend Prince's Celebration 2024 from June 20th to 24th, worth $4,000.
Contest ends: May 31, 2024
Entry limit: Single Entry
Eligible for Canadian Residents(Except: QC)